Managing up

5 not-so-often-shared ways to manage up and have a better relationship with your boss.

You want to manage up – but what you really mean is that you simply want to work well with your boss.

Who doesn’t? Especially when your boss is pestering you with questions via Slack after work-hours, or failing to give you enough time to complete projects…

You sigh and think yourself: “How do I manage up effectively?”

This is one of the most common questions I’m asked – and, unfortunately, one of the most common situations that you might face, whether you’re a manager, executive or individual contributor.

Based on research we’ve done over the past five years with hundreds of managers and employees, and the insights shared in our online leadership community, The Watercooler, here are the 5 distinct ways you can manage up to have a better relationship with your boss:

Share progress more often than you typically would.

Your boss is craving to know what you’re working on. We recently conducted a survey of 355 people and learned that the #1 piece of information that managers want to know is the progress that’s being made on a project. As a result, you’ll want to ask yourself:Am I sharing the progress I’m making day-to-day or week-to-week? You can also ask your boss directly: “How can I give you more visibility into my work?” or “Are there any decisions or projects you wish I were more transparent about?” Additionally, in Know Your Team in fact, we have a tool called “The Heartbeat” that helps you do this with little to zero effort – it’s an easy way to automate daily or weekly check-ins with your team. I highly recommend taking a peek if you feel like your team doesn’t have an effective process for sharing progress.

Uncover your boss’ work preferences (even if they don’t do the same for you).

We all have preferences around the way we like to work – including our boss. Make sure you spend time asking questions to your boss to figure out what theirs are. The more you know about how your boss likes to work (e.g., how they prefer to receive feedback, when they’re most productive during the day), the more you can adjust your own behavior to increase the likelihood of a positive relationship with them. It may seem frustrating (rightfully!) that you have to be the one to instigate this conversation, if they haven’t already (they are your manager, after all) – but some people need the nudge. You can provide it 🙂

Here are some of my favorite questions to ask around uncovering someone’s work preferences:

Where on the spectrum of extrovert to introvert would you place yourself?

What’s your preferred way to receive feedback, in terms of format?

What’s your preferred way to receive feedback, in terms of speed?

What’s your orientation toward conflict?

What time of day are you most productive?

How would you describe your communication style?

What motivates you the most?

Who is your hero? Why?

What do you consider your “super power”?

Who’s been the best coworker / team you’ve worked with? Why?

Who’s been the best boss / mentor you’ve ever had? Why?

When have you worked with someone and noticed it not going well?

What do you think you’re more sensitive about, compared to others?

What’s your biggest work-related pet peeves (i.e., that thing other people do that totally annoys you when you work with them)?

What would others who’ve worked with you say are your greatest strengths?

What would others who’ve worked with you say are your greatest weaknesses?

(Note: These are also fantastic questions to ask when onboarding a new hire, in general, and not just to your boss. )

Build trust through your actions, not just your words.

Let’s get real: Your boss might not trust you. Oftentimes, a boss’ micromanaging tendencies are derived from their lack of trust in your ability to follow through on something. Now, this may not be your fault by any means – your manager could be projecting their own past experiences onto you. But it does reveal that if you want a strong relationship with your boss, you must enable them to feel they can trust in your capabilities.

To be clear: You’re not trying to blow smoke or curry favor with your boss. Trust does not mean likability. Rather, you should be focused making sure your behavior matches your intention – that’s the best way to build trust. Your boss is going to give you more space the more you show them that they can give you that space. This means taking a close look and asking yourself: How well do I follow through on my word? The more closely that your actions mirror your words, the more likely your manager will have a greater degree of trust in you.

Foster real rapport.

Intuitively, we tend to have more positive relationships with people we feel interpersonally connected with. So, looking to form some sort of rapport with your boss is helpful to manage up, as well. This doesn’t mean you need to become best friends with them, do a whole in-depth reveal on your personal life, or ask them a bunch of corny icebreaker questions. Instead, it means you can share about what makes you tick, what you’re passionate about, what you like to do outside of work, etc… And, you can ask questions to uncover similar aspects of who your boss is, too. Here are some of my favorite questions to ask that you can consider asking over a lunch or coffee chat with your boss, beyond the typical icebreakers:

What was your first job?

What are you reading right now?

Who’s someone you really admire?

Seen any good movies lately you’d recommend?

Who had the most influence on you growing up?

What’s the best advice you’ve ever heard?

Been pleasantly surprised by anything lately?

Get crystal clear on expectations.

Possibly the most constructive way to manage up is to make sure you’re clear on what your manager expects of you. Without clear expectations, naturally, it’s easy to step on each other’s toes, misinterpret a comment, or be offended by a request. Instead, make it your mission to get clear on two things in particular: (1) What “success” looks like (2) How to communicate well to achieve “success.” Here are some questions you can ask to do this…

What things will I need have accomplished this year for you to view me in this role as “successful”?

What does quality work look like to you?

If I need your attention on something urgent, what form of communication do you prefer? (E.g., Slack, an email, a phone call)

What do you consider “urgent” versus “not urgent”?

If I have any feedback, how would they prefer you receive it: In person, in writing, over the phone, or during a video call?

If I have a suggestion about something, how would you prefer you receive it: In writing, in person, over the phone, or during a video call?

If I have a question, what form of communication should I pose the questions to you? (E.g., In writing, in person, over the phone, during a video call)

Remind yourself: Dissent is an obligation.

Managing up also means speaking up. Your manager is never going to know where you’re coming from and what you think if you don’t vocalize it. This can be daunting, not to mention implausible, if your manager isn’t receptive to feedback or your workplace environment is toxic. However, if you do perceive even a slight chance that your manager might be receptive, I suggest you take it – feedback can be delivered both honestly and kindly. To deliver difficult feedback well, here are a few phrases you can use…

“Would you be open to hearing some quick feedback around a few things I noticed?”

“I heard a few things on a call the other day that I thought we could talk through together — would you be open to that?”

“Happen to have time later today to chat around a few things I saw?”

“Would you want to sit down and talk about different ways we can both improve?”

“I’m sharing this because I want to team to succeed…”

“This is important to me because I care about the company’s direction as a whole…”

Take note: This is a general map, not a step-by-step guide, to manage up. You’ll have to assess, for yourself, your own manager’s propensity to be open to some of these questions and conversations.

However, most broadly, thinking about these 5 aspects – sharing progress, uncovering work preferences, building both trust and rapport, clarifying expectations, and sharing feedback – are things you can experiment with as you aspire to have a strong working relationship with your boss.

The ball is in your court, more than you might think.

Claire is the CEO of Know Your Team – software that helps you avoid becoming a bad boss. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

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